Tetrahydrofuran → HCID 86676709, compound

HRID 711601Notes

Reaction equation

HRID 711601 reaction equation
[Br-:1].[Br-:2].[Br-].C(CC[P+]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.[C:28]([CH2:31][CH2:32][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:30])=O.[C:52]([CH2:55][CH2:56][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.[O:76]1CCCC1>>[Br:1][CH:56]([C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:28][CH2:31][CH2:32][Br:2])=[CH:26][CH:27]=1)[C:55](=[O:76])[CH3:52]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 57350967(2-Carboxyethyl)(triphenyl)phosphanium bromide (1/1)

Product 1

HCID 86676709HCID 86676709, compound

Procedure

To a solution of the product from Example 1C (865 mg, 3.19 mmol) in anhydrous tetrahydrofuran (30 mL) was slowly added a tetrahydrofuran (10 mL) solution of (2-carboxyethyl)triphenylphosphonium tribromide (1.85 g, 3.19 mmol) at 0° C. The mixture was then stirred at ambient temperature for 2 hours. The mixture was partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was washed with additional ethyl acetate. The organic fractions were combined, washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.31 (s, 3H), 2.37-2.27 (m, 2H), 3.60 (t, J=6.4 Hz, 2H), 4.11 (t, J=5.8 Hz, 2H), 5.42 (s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.36 (d, J=8.8 Hz, 2H); MS (DCI/NH3) m/z 366 (M+NH4)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. washthe aqueous layer was washed with additional ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c98440a2b5874719ba66b14ffa078b4a
Source dataset
uspto-grants-2015_11
Patent number
US09181275B2

Reaction notes

Loading…